First Time
by AshestoRoses
Summary: A first time story, just not in the traditional sense.


It's 8pm, and Tom Feldman's been in with Harvey for the last forty minutes. It's excruciating really, to sit here, knowing what's in store for this evening. I wish he'd just leave! Not that I would do anything as undignified at fidget or sigh. Nope. Not me.

Much later, on my stomach on Harvey's bed, looking out onto the nighttime skyline, my wrists cuffed to his headboard, and the man himself kneeling behind me, it's such a relief to be able to turn all the planning and calculating off for the night.

His hands are splayed against my lower back, just resting for now.

"Will you cry for me tonight Donna?"

I jerk slightly in shock, tugging against my bonds, just realizing what kind of night he's asking for.

"Donna, Donna…" I can hear the amusement in his voice. That satisfaction he gets from knowing he's hit a tender spot.

I feel a hand slip between my legs and under me, urging me to lift up. Efficiently, he slides a pillow under me, exposing me to his gaze.

"Colour?"

My breath hitches, and I say, "Green."

"Good girl." Approving. Content.

I feel his hands moving up and down my back now, petting, gentling me. All of a sudden the room feels warmer.

"A little cold now." Almost immediately, I feel a cool spot on my lower back. Lube. I shiver. His fingers scooping up the slippery substance and almost immediately resting against my anus.

"Yellow." The response is almost visceral, and as I know will happen, his fingers withdraw immediately, his hands going back to their default position, splayed against my lower back, comforting.

His voice is serious now, no longer playful. "Need me to uncuff you?" I feel his thumb rubbing lightly against my skin.

I shake my head, annoyed with myself for what feels like an over-reaction now. Hushed, I say, "Just startled?" I can feel myself blushing, and damn my pale, pale skin, he's probably seeing the back of my neck turn red. A grown woman, and somehow, I've never had someone want to touch me there.

He's silent for long seconds and then he's no longer touching me and I'm _mortified _now and somehow just can't stop the whimper (whimper!) that escapes me.

"Easy, kitten. I'm still here." And suddenly he's laying down right beside me, looking into my eyes.

"Should I be channeling Madonna here?" He runs a hand up and down my back though, and his eyes are warm.

I try and relax, but… "It's silly right? I mean I'm a grown woman in cuffs and I have a _safeword,_ and you just asked me if I'd _cry _ for you… and I said _yes_! I've just never…"

He raises and eyebrow and says, "Never?"

I shake my head.

He reaches up to uncuff me, and I can't help but move my hands as far away from him an possible, not wanting him to take them off and stop completely. I feel like I've failed, and I turn my face into the bed, hiding.

He just follows though, unfastening and letting the hand-tooled leather fall away. Then, he's urging me wordlessly into his arms, tugging until my face is buried in his chest instead, chuckling as he says, "Lovely, lovely Donna. I'm going to have fun with you."

I reach out and nip at his chest lightly with my teeth, warningly. I feel him jump and then he's laughing, shaking with mirth. This easy handling works though, lifts me from that uncomfortable place where I feel as though I'm not quite good enough, experienced enough to be in his bed.

When he's done laughing at me, he nuzzles into the top of my head for a second before he starts talking.

"Do you want me to?"

And there it is, his offer to make that particular fantasy a reality. And it's always been a fantasy. He's talking again though, and I'm taken from my internal musings.

His words are soft, gentle, but shocking, "I'd just play for a bit, getting you used to being touched back there. When you can take a finger easily, we'll switch gears a little bit." He hugs me a little closer to him. "I'll want you all cleaned out for me, so I'll give you an enema, a nice warm, gentle one. Have you ever had one before?"

And now my face really is flaming, and I'm tensed in his arms.

I look up at him and say, "When I was younger…" And it hadn't been pleasant at all. All cold and clinical and _painful _and uncomfortable and _embarrassing. _

He sees it in my face though, of course he does, and shakes his head as he says, "This won't be like that. Some people take them just because they like the feeling of being full and warm. If you're tense, it might cramp a little, but we'll take it nice and slow, so it shouldn't be a problem."

I nod and wait, wanting to see where he'll take this, and suddenly, I'm aroused again, aware of his naked body against mine, and again, damn the man and his perceptiveness, he sees it.

"And when it's all done, we'll play. I'll open you up, nice and slow and easy. You'll whimper, and moan, and maybe even beg." He lets a hand drift down my back and rest on my ass, cupping it. "And when you're so ready you're aching with it, when you're relaxed and stretched enough, that's when it'll happen." He leans down to steal a kiss. "Sound good?"

Hoarsely, "Yeah…" I clear my throat. "I'd like that." I push my ass back and into his hand.

I feel his hand squeeze down and then leave. He uses the sheet to wipe away the slick mess of lube on my lower back from earlier, and there's a faint 'snick' of the lube being uncapped again.

"Colour?" He looks at me, knowing that sometimes my mouth's said yes, but my body still balks when I'm nervous.

"Green." My eyes are wide open now though, and I can't tell if it's nerves or arousal I'm feeling.

He's smiling as he runs a slick finger down my crease. I shiver and gasp, shifting slightly as I feel myself get wetter all of a sudden.

"I can't believe no one's ever done this with you… " His eyes are half lidded, and dark with lust. I can feel his fingers drifting between my cheeks, probing, touching, soothing, all at the same time.

All of a sudden I can't wait. The anticipation's killing me, and I hear myself let out a slight whine of frustration. "Please Harvey, let me feel it?"

Immediately, as if that's the moment he's been waiting for, his finger comes to rest against my hole. "Deep breath now."

I take a deep breath in, inhaling the luxurious, delicious smell of him, loving how he always smells so damn good. He does nothing though, and I clench slightly in nervous anticipation. When I can't hold it any longer, I breathe out and relax, and feel his finger press in. "Ohhh….." My toes curls at the strange sensation, not-quite-good and not-quite-bad at the same time.

"There… nice and easy." I feel his finger rock ever-so-slightly inside me, and he's watching my face for a reaction. I clench and unclench experimentally around his finger and he ducks his head to claim a kiss and suck lightly on my bottom lip. "Okay?"

Too overwhelmed to speak, I just nod and lean back in to kiss him. Time passes in a haze of kisses and lube and just that one finger moving in and out, twisting, turning, pressing, rocking. Somewhere along the way, I bend a knee and lift my leg up and over his to give him more room. He uses his free hand to touch me too, rolling a nipple or cupping my face.

It feels like forever, and I've almost forgotten through the haze of arousal what else he promised he'd do tonight. When he pulls away slightly and smiles though, I do remember, and I feel myself clamp down against him.

"Shh… nothing scary's going to happen here Donna… you're okay." And it's those words, soothing and comforting that none of his opposing counsel or colleages or associates would ever imagine come out of this man's mouth. "Trust me?"

And I relax, because I really do.

"Good girl."

He leaves the bed then, heading off to the bathroom. I hear water running and other noises, and it's just a few minutes when he's hanging an enema bag on the sturdy stem of the bedside, wall-mounted lamp, well within my view. When he sits down, his back against the headboard, watching me watch the ominous-looking contraption, he pats his lap. "Come on up here love."

As I settle over his lap, he just caresses my ass, reminding me that I've been in this position many, many times before. Granted, it usually ends with a spanking that's got me writhing, pleading, and squirming, my ass red and glowing. Still. It's familiar. This time though, he wastes no time parting my cheeks, exposing me to his view, and I feel his slicked finger against me. It's not quite so foreign this time when he slips his finger in, making sure I'm slick and relaxed enough for him.

When he's satisfied, I see him pick up the nozzle.

"It's big!"

I can almost hear him rolling his eyes as he says, "Easy now big baby!" Contrary to the dismissive quality of his words though, he holds it up so I can see. Up close, it's really not much wider than his finger. I nod, accepting, and he's moving it behind me almost immediately.

He doesn't give me time to panic before he's easing the lubed tip in and pressing forward so it's sinking into me. It's really not much bigger than his finger, and I probably am being a baby, but it's cold, hard, and _foreign._ I writhe a tad bit, and he's back to soothing, murmuring nonsense things, comforting things, about how good I'm being for him, how I look so pretty taking this, and how it's almost in. His hand is warm and heavy on my lower back, anchoring me. When the flared base enters me, I gasp, but it's settling into me before it can even begin to feel painful or bad in any way. It's just… different… from anything I've ever felt before.

When it settles fully inside me, I feel a little overwhelmed and take a few seconds to just breathe and look out over the city lights. He lands a gentle smack against my bum and I see him unclamp the hose.

Unlike what I expected, it's a subtle feeling, and he's right, it's just a warmth more than anything else. He raises a leg and I'm tipping slightly forward, probably to help the fluid flow into me.

"You have the most perfect ass, did you know that? All silky skin and perfectly shaped. Luscious."

Suddenly, though, I feel an uncomfortable cramping, and I reach out to grip Harvey's leg. He stops the flow and croons at me, his hand slipping under my belly to rub and soothe, and his leg tipping me just a tad farther. Softly, "Cramp?"

"Not really bad… just a little uncomfortable?" It goes on like that for long minutes. Warm water flowing into me until it gets uncomfortable, him stopping the flow until I adjust, and then starting it up again until it's all done. Meanwhile, he touches me, talks to me, and reassures me that I'm doing well. It's intimate and close, but I know he's keeping me distracted, keeping me from freaking out.

The last time he clamps off the tube, the bag's empty, but I don't even really notice until a few minutes go by and he wiggles the tube a tad bit. The rocking feels strange, but good at the same time. "I'm going to ease it out, okay?"

Immediately, I tense up. "What if I can't…" And I'm blushing again and hoping he won't make me say it out loud, but this time he just waits for me to finish.

"What if you can't… finish the sentence, love." He reaches out and tucks my hair behind my ear so he can see my face clearly, so I can't hide.

Whispering, "What if I can't hold it?"

Nodding, "Understandable question, but it's not a lot of solution, and it's just going to be until we get you to the washroom."

I close my eyes, reassured by his competence and the control he has over this situation, but still overwhelmed. Softly, "Okay."

I feel the nozzle sliding out and find that he was right. It's not particularly uncomfortable, and as I ease off his lap and the bed, he immediately pulls a sheet up and around me so I'm not cold. When we reach the washroom though, I balk. "You're not coming in, right?"

"That would make you uncomfortable?" He reaches to turn on the lights. Like in the rest of the condo, they're on a dimmer, so it's not jarring.

Yes! "Yes, it would make me uncomfortable!"

Shaking his head and chuckling, "You're right, I'm not coming in. Not because it makes me uncomfortable—For the record, it doesn't—but because you don't look like you're going to freak out in there. And… you have a relationship with my shower that's deeply lustful, and I'm not sure I'd like to try and compete." Smirking and stepping back, "Let it out, shower, and come on back when you're ready, okay?" Then, seriously, stepping back towards me, "Don't strain okay?" A hand on my back, "Just relax and let it happen."

I nod absently, my mind already on his glorious shower.

When I step back into his bedroom, the lights are dimmer, and there's a glass of juice, a small plate of cheese and crackers set up on the bedside table and Harvey's sitting up in bed, going through email on his phone. He sets it aside and smiles though, as I straddle his lap, facing him.

He says nothing. Leaning over to the side table, he pulls out a small pair of nipple clamps from an ebony box he keeps there.

Breathless, "Do you have to do that? I mean, it's not.."

He leans up to capture my mouth in a kiss while simultaneously rolling my left nipple between two fingers. Against my lips, "I like watching you squirm and whimper and get all stoned on endorphins. Also.." He pinches down lightly with his fingers. "I don't _have_ to do anything."

"Ohhh…" I watch nervously as he brings the open jaws towards me and lets the teeth bite down in a smooth, practiced motion. "Ahh! Oh, god, please Harvey!" My hands come up instinctively to flick it off, but he just captures them in his."

"Shh… Are you telling me to stop, Donna?"

He releases one of my hands and trails down my stomach to tease between my legs.

I gasp and press forward against his fingers. "Would you?"

"Are you asking me to?" He releases my other hand, grasps the clamps, and turns it clockwise, about 90 degrees.

Shivering at how good it feels, I cry out, "No!"

He tugs at it lightly before letting it go and sliding two fingers of his other hang into my vagina, crooking forward and pressing up against my g-spot. "No, don't hurt you? Or no, don't stop?" His thumb comes to rest against my clit hood, massaging gently.

I groan and my head tips back. "No, don't stop."

And immediately, he's pulling on the little metal fucker again, tugging it away from my body, and this time it _hurts_! "Owwwwww… ow ow ow ow, please! Please, no more!" I drop my head to his shoulder and he turns his head to kiss the side of my neck, not letting up on the pressure.

"There you go, love. You suffer so beautifully for me, hmm?" He lets go again, and I sag against him, gasping for breath.

"One more now, okay?"

I shake my head, but I know it's futile, and when I feel his fingers slip out from inside me, I shiver at the sensation, but also with nerves.

As I ease myself away from hiding in his shoulder, he rolls my right nipple between his fingers. This one though, he clamps a little closer to the tip, so it stings more, and feels almost unbearable.

"No, no no no, no Harvey, please" He holds my hands tightly now, and I struggle against him. "Please, it's too much!"

"Easy, easy, Donna. Look at me."

My eyes are clenched shut, and I whimper.

"_Look at me._"

I open my eyes and look into his half-lidded, lust-darkened eyes, and I let out a small sob. "Just breathe for me Donna, and hang in there for a few seconds. It'll get better, I promise."

I tremble, and relax when I realize he's right. This _always _happens. It's that initial shock, before the buzz kicks in.

"There you go." He kisses my knuckles. "Beautiful. Colour?"

Panting, "Green."

He's still holding my hands, and I'm startled when he pushes forward towards me, tumbling us both backwards, and ending with me lying back on the bed. We're kissing and touching each other and he always feels so good on top of me.

"So… question for you…" He leans down and sucks briefly on the right nipple clamp. "How shall I take these little buggers off?"

I groan and bring my knees up so my feet are flat on the bed. "How?... What?"

Chuckling, he flicks it with his tongue. "Yup how. As in slowly? Quickly? He presses a lubed finger (how did he even get the lube so quickly?) against my hole though, and I'm completely distracted. I startle and flinch upwards and away.

Murmuring, "Easy, easy, I'm not gonna hurt you there." He keeps contact, even though I've moved, and when I relax a little, I feel his well-lubed fingers enter me, slipping into such a private place. "Good… that's it… So, any ideas?"

"What? Ideas about what?" I'm lost, and so consumed by what's going with my body.

He keeps his fingers moving inside me, stretching, rubbing, and rocking in and out. "The clamps, Donna. Keep up here."

I raise myself up on my elbows and try to shake off the haze of arousal a little. "W-What about them?" I groan almost immediately though, since he's rubbing tiny, tiny little circles around my clit now, using his free hand.

"How to you want the clamps to come off Donna? Quickly? Or pulled off slowly?" He leans down and kisses my belly, looks up, and says casually, "Two fingers now, okay?" And there it is, a slightly fuller, more intense feeling. As his fingers enter me, I relax, letting myself feel the sensation.

"Well done sweetheart. You're doing so well for me."

Suddenly, I can't stand it, and I look into his eyes, "Harvey, please, I don't need you to distract me with the clamps." I swallow. "I just want to feel it, enjoy it, this first time."

His smile is bright, the kind of expression even his closest friends rarely get to see from him, and he nods, once. When he speaks, his voice is approving and his hands have stilled inside me. "There's the confidence I'm looking for Donna. You've spent the last hour doubting your place here in my bed. Asking yourself if you're good enough, interesting enough… Most distressingly—ah, ah, yes, I have emotions too—most distressingly, you're wondering if you're going to be able to take it." He pauses. "It's not an endurance test, Donna, and you just figured that out. You'll either enjoy it, or you won't, but you don't need me to distract you from it, as if it's a basically distasteful or scary thing we're doing."

I say nothing for a second, and then just can't hold it back. I laugh and reach out to flick his ear.

"Hey, oww!"

"Shut up, and fuck me Mr. Specter!"

Rubbing his ear, "Gladly, Ms. Paulson."

Sobering, "Thanks, Harvey."

Smiling, he nods. "You're welcome." Then, his smirk turns evil. "So, basically, all this was to tell me you want me to take them off quickly?"

"What?" I look down. "Oh, shit."

He reaches out and takes a hold of the clamp on my right nipple, and follows when I try to twist away from him. Without a pause, he presses the jaws open. For a second nothing happens, and then I'm keening in pain as the blood rushes back. "Harveyyyyy…"

He says nothing, but he does cover the abused nub with his mouth, suckling, helping me process it. Damn the man for his ability to multi-task though, because as he's doing that, he releases the second one too.

"Oh god, bastard!" I clutch his shoulders.

He looks up. "What did you just say to me?"

"Sadistic bastard. You. Harvey Specter. Now, put your mouth back to good use!"

Smirking, he does, and before I know it, I'm riding his fingers as he stretches me open. Two, then three fingers, his free hand rubbing and teasing my clit, and his mouth kissing and murmuring to me.

By the time he's ready to enter me, I've come three times, my muscles are so relaxed, and I feel exhausted in all the best ways. By the time he leans over me, presses his cock right up against my hole, and tells me to relax for him, I'm so ready, I whine out and clutch at him, begging wordlessly.

He fucks me, and like everything else he does, he does it well.


End file.
